EP3674291A1 - Cyclische aminverbindung und schädlingsbekämpfungsmittel - Google Patents

Cyclische aminverbindung und schädlingsbekämpfungsmittel Download PDF

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Publication number
EP3674291A1
EP3674291A1 EP18848338.2A EP18848338A EP3674291A1 EP 3674291 A1 EP3674291 A1 EP 3674291A1 EP 18848338 A EP18848338 A EP 18848338A EP 3674291 A1 EP3674291 A1 EP 3674291A1
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group
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EP18848338.2A
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English (en)
French (fr)
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EP3674291A4 (de
Inventor
Fumiya NISHIO
Jun Iwata
Satoshi Makino
Takao Iwasa
Koichi Hirata
Isami Hamamoto
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Nippon Soda Co Ltd
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Nippon Soda Co Ltd
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Priority to EP21172157.6A priority Critical patent/EP3889137A1/de
Publication of EP3674291A1 publication Critical patent/EP3674291A1/de
Publication of EP3674291A4 publication Critical patent/EP3674291A4/de
Withdrawn legal-status Critical Current

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/86—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
    • A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • A61K31/5355—Non-condensed oxazines and containing further heterocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • A61K31/5375—1,4-Oxazines, e.g. morpholine
    • A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
    • A61K31/541—Non-condensed thiazines containing further heterocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/14—Ectoparasiticides, e.g. scabicides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/84—Nitriles
    • C07D213/85—Nitriles in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/10—Spiro-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/10—Spiro-condensed systems
    • C07D491/107—Spiro-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C—CHEMISTRY; METALLURGY
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/10—Spiro-condensed systems
    • C07D491/113—Spiro-condensed systems with two or more oxygen atoms as ring hetero atoms in the oxygen-containing ring
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    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/10—Spiro-condensed systems

Definitions

  • the present invention relates to a cyclic amine compound and a pest control agent. Furthermore, the present invention relates to a cyclic amine compound that has excellent insecticidal and/or acaricidal activity and excellent safety and that can be synthesized industrially advantageously, and to a pest control agent containing the same as an active ingredient thereof.
  • Patent Document 1 discloses compounds of formula (A) or (B) shown below. These compounds have been shown to be useful in insecticides or acaricides.
  • Patent Document 1 WO 2015/032280 A1
  • the present invention aims to provide a cyclic amine compound which is excellent in pest control activity, particularly insecticidal and/or acaricidal activity, is excellent in safety, and can be synthesized in an industrially advantageous manner, and provide a pest control agent containing the cyclic amine compound as an active ingredient thereof.
  • the present invention encompassing the following aspects has been completed as a result of studying to solve the above-described problems.
  • a cyclic amine compound according to the present invention makes it possible to control pests that cause problems in agricultural crops and hygiene.
  • the cyclic amine compound particularly makes it possible to control agricultural insect pests and acarians at a low concentration effectively.
  • the cyclic amine compound makes it possible to effectively control ectoparasites that cause harm to humans or livestock.
  • a cyclic amine compound according to the present invention is a compound of formula (I) (hereinafter, may be indicated as compound (I)) or a salt of the compound (I).
  • the term "unsubstituted" refers to a group consisting of a mother nucleus. In the case where only the name of a group serving as a mother nucleus is provided, this refers to "unsubstituted” unless specifically indicated otherwise.
  • substituted means that any hydrogen atom of a group serving as a mother nucleus is substituted with a group having a structure that is identical to or different from the mother nucleus.
  • a substituted is another group bound to a group serving as the mother nucleus.
  • the number of substituent may be one or two or more. Two or more substituents may be identical to or different from each other.
  • any hydrogen atom in the "substituent" may also be substituted with another group having a different structure.
  • C1-6 means that the number of carbon atoms constituting a group serving as a mother nucleus is 1 to 6. The number of carbon atoms does not include the number of carbon atoms constituting a substituent. For example, an ethoxybutyl group is classified as a C2 alkoxy C4 alkyl group.
  • the "3- to 6-membered heterocyclyl group” is a group formed by removing one hydrogen atom from an arbitrary ring atom of a "3- to 6-membered heterocyclic compound", which is a 3- to 6-membered cyclic compound containing, as an atom constituting a ring (which may be referred to as ring member atom), 1 to 4 hetero atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom.
  • the "3- to 6-membered heterocyclyl group” may be described as a "3- to 6-membered heterocyclyl group containing, as a ring member atom, 1 o 4 hetero atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom".
  • the heterocyclyl group may be monocyclic or polycyclic. If at least one ring of a polycyclic heterocyclyl group is a hetero ring, remaining rings thereof may be any of saturated alicyclic rings, unsaturated alicyclic rings and aromatic rings. Examples of the "3- to 6-membered heterocyclyl group” include 3- to 6-membered saturated heterocyclyl groups, 5- to 6-membered heteroaryl groups, and 5- to 6-membered partially unsaturated heterocyclyl group.
  • Examples of the 3- to 6-membered saturated heterocyclyl group include an aziridinyl group, an epoxy group, a pyrrolidinyl group, a tetrahydrofuranyl group, a thiazolidinyl group, a piperidyl group, a piperazinyl group, a morpholinyl group, a dioxolanyl group, and a dioxanyl group.
  • Examples of the 5-membered heteroaryl group include a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group, and a tetrazolyl group.
  • 6-membered heteroaryl group examples include a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, and a triazinyl group.
  • Ar represents a substituted or unsubstituted C6-10 aryl group.
  • a C6-10 aryl group as Ar is a group formed by removing one hydrogen from a ring of a monocyclic or polycyclic aromatic hydrocarbon.
  • Examples of the C6-10 aryl group include a phenyl group and a naphthyl group, and the C6-10 aryl group is preferably a phenyl group.
  • Examples of a substituent on the C6-10 aryl group include halogeno groups, substituted or unsubstituted C1-6 alkyl groups, substituted or unsubstituted C2-6 alkenyl groups, substituted or unsubstituted C2-6 alkynyl groups, substituted or unsubstituted C1-6 alkoxy groups, substituted or unsubstituted C2-6 alkenyloxy groups, a formyl group, substituted or unsubstituted C1-6 alkylcarbonyl groups, substituted or unsubstituted C1-6 alkoxycarbonyl groups, substituted or unsubstituted C1-6 alkylthio groups, substituted or unsubstituted C1-6 alkylsulfinyl groups, substituted or unsubstituted CI-6 alkylsulfonyl groups, substituted or unsubstituted C3-8 cycloalkyl groups, substituted or unsubstituted C6-10 aryl groups
  • R 31 represents a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group
  • R 32 represents a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group.
  • halogeno group as a substituent on the C6-10 aryl group include a fluoro group, a chloro group, a bromo group, and an iodo group.
  • the "C1-6 alkyl group" as a substituent on the C6-10 aryl group may be linear or branched.
  • the alkyl group include a methyl group, an ethyl group, a n-propyl group, a n-butyl group, a n-pentyl group, a n-hexyl group, an i-propyl group, an i-butyl group, a s-butyl group, a t-butyl group, an i-pentyl group, a neopentyl group, a 2-methylbutyl group, a 2,2-dimethylpropyl group, and an i-hexyl group.
  • Examples of the "C2-6 alkenyl group" as a substituent on the C6-10 aryl group include a vinyl group, a 1-propenyl group, a 2-propenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-methyl-2-propenyl group, a 2-methyl-2-propenyl group, a 1-pentenyl group, a 2-pentenyl group, a 3-pentenyl group, a 4-pentenyl group, a 1-methyl-2-butenyl group, a 2-methyl-2-butenyl group, a 1-hexenyl group, a 2-hexenyl group, a 3-hexenyl group, a 4-hexenyl group, and a 5-hexenyl group.
  • Examples of the "C2-6 alkynyl group" as a substituent on the C6-10 aryl group include an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group; a 2-butynyl group, a 3-butynyl group, a 1-methyl-2-propynyl group, a 2-methyl-3-butynyl group, a 1-pentynyl group, a 2-pentynyl group, a 3-pentynyl group, a 4-pentynyl group, a 1-methyl-2-butynyl group, a 2-methyl-3-pentynyl group, a 1-hexynyl group, and a 1,1-dimethyl-2-butynyl group.
  • Examples of the "C1-6 alkoxy group" as a substituent on the C6-10 aryl group include a methoxy group, an ethoxy group, a n-propoxy group, a n-butoxy group, a n-pentyloxy group, a n-hexyloxy group, an i-propoxy group, an i-butoxy group, a s-butoxy group, a t-butoxy group, and an i-hexyloxy group.
  • Examples of the "C2-6 alkenyloxy group" as a substituent on the C6-10 aryl group include a vinyloxy group, an allyloxy group, a propenyloxy group, and a butenyloxy group.
  • C1-6 alkylcarbonyl group as a substituent on the C6-10 aryl group include an acetyl group and a propionyl group.
  • C1-6 alkoxycarbonyl group as a substituent on the C6-10 aryl group include a methoxycarbonyl group, an ethoxycarbonyl group, a n-propoxycarbonyl group, an i-propoxycarbonyl group, and a t-butoxycarbonyl group.
  • C1-6 alkylthio group as a substituent on the C6-10 aryl group include a methylthio group, an ethylthio group, a n-propylthio group, a n-butylthio group, a n-pentylthio group, a n-hexylthio group, and an i-propylthio group.
  • C1-6 alkylsulfinyl group as a substituent on the C6-10 aryl group include a methylsulfinyl group, an ethylsulfinyl group, and a t-butylsulfinyl group.
  • C1-6 alkylsulfonyl group as a substituent on the C6-10 aryl group include a methylsulfonyl group, an ethylsulfonyl group, and a t-butylsulfonyl group.
  • C1-6 alkyl group Preferable examples of a substituent on the "C1-6 alkyl group", “C2-6 alkenyl group”, “C2-6 alkynyl group”, “C1-6 alkoxy group”, “C2-6 alkenyloxy group”, “C1-6 alkylcarbonyl group”, “C1-6 alkoxycarbonyl group”, “C1-6 alkylthio group”, “C1-6 alkylsulfinyl group”, or “C1-6 alkylsulfonyl group”, which are substituents on the C6-10 aryl group, include: halogeno groups such as a fluoro group, a chloro group, a bromo group, and an iodo group; C1-6 alkoxy groups such as a methoxy group, an ethoxy group, a n-propoxy group, an i-propoxy group, a n-butoxy group, a s-butoxy group, an i-butoxy group, and a t-butoxy group;
  • Examples of the "C3-8 cycloalkyl group" as a substituent on the C6-10 aryl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group.
  • C6-10 aryl group as a substituent on the C6-10 aryl group include a phenyl group and a naphthyl group.
  • Examples of the "5- or 6-membered heteroaryl group" as a substituent on the C6-10 aryl group include: 5-membered heteroaryl groups such as a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isooxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group, and a tetrazolyl group; and 6-membered heteroaryl groups such as a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, and a triazinyl group.
  • 5-membered heteroaryl groups such as a pyrrolyl group, a furyl group, a thi
  • C6-10 aryloxy group as a substituent on the C6-10 aryl group include a phenoxy group, and a naphthoxy group.
  • Examples of the "5- or 6-membered heteroaryloxy group" as a substituent on the C6-10 aryl group include 5- or 6-membered heteroaryloxy groups such as a thiazolyloxy group, and a pyridyloxy group.
  • a substituent on the "C3-8 cycloalkyl group”, “C6-10 aryl group”, “5- or 6-membered heteroaryl group”, “C6-10 aryloxy group”, or “5- or 6-membered heteroaryloxy group”, which are substituents on the C6-10 aryl group include: halogeno groups such as a fluoro group, a chloro group, a bromo group, and an iodo group; C1-6 alkyl groups such as a methyl group, an ethyl group, a n-propyl group, an i-propyl group, a n-butyl group, a s-butyl group, an i-butyl group, a t-butyl group, a n-pentyl group, and a n-hexyl group; C1-6 haloalkyl groups such as a chloromethyl group, a chloroethyl group,
  • R 31 represents a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group
  • R 32 represents a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group.
  • Examples of the "substituted or unsubstituted Cl-6 alkyl group" as R 31 and R 32 include the same groups as those mentioned above.
  • the substituent on the C6-10 aryl group is preferably a halogeno group, a substituted or unsubstituted C1-6 alkyl group (more preferably a C1-6 alkyl group which may be substituted with a halogeno group), a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C1-6 alkoxy group (more preferably a C1-6 alkoxy group which may be substituted with a halogeno group), a substituted or unsubstituted C1-6 alkylthio group (more preferably a C1-6 alkylthio group which may be substituted with a halogeno group), a substituted or unsubstituted C3-8 cycloalkyl group (more preferably a C3-8 cycloalkyl group which may be substituted with a halogeno group), a substituted or unsubstituted C6-10 aryl group (more preferably a a C
  • R 1 in the formula (I) represents a cyano group or a substituted or unsubstituted thiocarbamoyl group.
  • R 2 in the formula (I) represents a hydrogen atom, a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a hydroxyl group, or a substituted or unsubstituted C1-6 alkoxy group.
  • R 3 in the formula (I) represents a hydrogen atom, a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C3-8 cycloalkyl group, a hydroxyl group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- or 6-membered heteroaryl group.
  • substituted thiocarbamoyl group examples include mono or di C1-6 alkyl-substituted thiocarbamoyl groups, such as a methylthiocarbamoyl group, a dimethylthiocarbamoyl group, and an ethyl(methyl)thiocarbamoyl group.
  • halogeno group substituted or unsubstituted C1-6 alkyl group
  • substituted or unsubstituted C1-6 alkoxy group as R 2 and R 3 include the same groups as those specifically mentioned as Ar.
  • a C1-6 alkylthio group, a C1-6 alkylsulfinyl group, or a C1-6 alkylsulfonyl group is mentioned as a substituent of the "substituted C1-6 alkyl group" as R 3 .
  • Examples of the "substituted or unsubstituted C3-8 cycloalkyl group", “substituted or unsubstituted C6-10 aryl group", or “5- or 6-membered heteroaryl group” as R 3 include the same groups as those specifically mentioned as Ar.
  • R 2 is preferably a hydrogen atom
  • R 3 is preferably a hydrogen atom, a halogeno group, a substituted or unsubstituted C1-6 alkyl group (preferably a C1-6 alkyl group which may be substituted with a halogeno group, a C1-6 alkoxy group, a C1-6 alkylthio group, a C1-6 alkylsulfinyl group, or a C1-6 alkylsulfonyl group), a substituted or unsubstituted C3-8 cycloalkyl group, a substituted or unsubstituted C1-6 alkoxy group, or a substituted or unsubstituted C6-10 aryl group (preferably a phenyl group).
  • Q represents a cyclic amino group of formula (II-a), a cyclic amino group of formula (II-b), or a cyclic amino group of formula (II-c).
  • an arrow indicates a binding position.
  • p 1 indicates the number of methylenes in parentheses and is 0 or 1, and preferably 1
  • p 2 indicates the number of methylenes in parentheses and is an integer of 0 to 2, and preferably 1.
  • the cyclic amino group of formula (II-a) is represented by formula (II-a-1), when p 1 is 1 and p 2 is 1.
  • X 1 indicates a substituent on the cyclic amino group, and is a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a hydroxyl group, a substituted or unsubstituted C1-6 alkylsulfonyloxy group, or a substituted or unsubstituted C1-6 alkylthio group
  • m indicates the number of X 1 and is an integer of 0 to 4 (preferably 0)
  • X 2 is a hydrogen atom, a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a hydroxyl group, or a substituted or unsubstituted C1-6 alkoxy group.
  • halogeno group substituted or unsubstituted C1-6 alkyl group
  • substituted or unsubstituted C1-6 alkylthio group substituted or unsubstituted C1-6 alkylthio group
  • C1-6 alkylsulfonyloxy group examples include a methylsulfonyloxy group, an ethylsulfonyloxy group, and a t-butylsulfonyloxy group.
  • a substituent on the "C1-6 alkylsulfonyloxy group” include halogeno groups such as a fluoro group, a chloro group, a bromo group, and an iodo group.
  • halogeno group substituted or unsubstituted C1-6 alkyl group
  • substituted or unsubstituted C1-6 alkoxy group substituted or unsubstituted C1-6 alkoxy group
  • X 2 preferably represents a hydrogen atom, a halogeno group, a hydroxyl group, or a substituted or unsubstituted C1-6 alkoxy group.
  • Y represents a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkylcarbonyl group, a substituted or unsubstituted C1-6 alkoxycarbonyl group, a thiocarbamoyl group, a substituted or unsubstituted C1-6 alkylthio group, a substituted or unsubstituted C1-6 alkylsulfinyl group, a substituted or unsubstituted C1-6 alkylsulfonyl group, a substituted or unsubstituted C3-8 cycloalkyl group, a substituted or unsubstituted C6-10 arylcarbonyl group, a group of
  • Examples of the group of R g R h N-SO 2 - include a N-methylaminosulfonyl group, a N,N-dimethylaminosulfonyl group, a N-ethyl-N-methylaminosulfonyl group, a N-methoxy-N-methylaminosulfonyl group, and a pyrrolidin-1-yl sulfonyl group, a N-(4-chlorophenyl)aminosulfonyl group, and a N-(4-chlorophenylmethyl)aminosulfonyl group.
  • an arrow indicates a binding position.
  • p 1 indicates the number of methylenes in parentheses and is 0 or 1, preferably 1
  • p 2 indicates the number of methylenes in parentheses and is an integer of 0 to 2, preferably 1.
  • the cyclic amino group of formula (II-b) is represented by formula (II-b-1), when p 1 is 1 and p 2 is 1.
  • X 1 indicates a substituent on the cyclic amino group, and is a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a hydroxyl group, a substituted or unsubstituted C1-6 alkylsulfonyloxy group, or a substituted or unsubstituted C1-6 alkylthio group
  • m indicates the number of X 1 and is an integer of 0 to 4 (preferably 0).
  • halogeno group substituted or unsubstituted C1-6 alkyl group
  • substituted or unsubstituted C1-6 alkylthio group substituted or unsubstituted C1-6 alkylthio group
  • C1-6 alkylsulfonyloxy group examples include a methylsulfonyloxy group, an ethylsulfonyloxy group, and a t-butylsulfonyloxy group.
  • a substituent on the "C1-6 alkylsulfonyloxy group” include halogeno groups such as a fluoro group, a chloro group, a bromo group, and an iodo group.
  • Examples of the "C2-6 alkylene group" as Z include a dimethylene group, a trimethylene group, a tetramethylene group, and a pentamethylene group.
  • Examples of a substituent on the "C2-6 alkylene group” include: halogeno groups such as a fluoro group, a chloro group, a bromo group, and an iodo group; and C1-6 alkyl groups such as a methyl group, an ethyl group, a n-propyl group, an i-propyl group, a n-butyl group, a s-butyl group, an i-butyl group, a t-butyl group, a n-pentyl group, and a n-hexyl group.
  • the substituent is preferably a halogeno group.
  • Examples of the "C1-6 alkylene group" as G a include a methylene group, a dimethylene group, a trimethylene group, a tetramethylene group, and a pentamethylene group.
  • Examples of a substituent on the "C1-6 alkylene group” include: halogeno groups such as a fluoro group, a chloro group, a bromo group, and an iodo group; and C1-6 alkyl groups such as a methyl group, an ethyl group, a n-propyl group, an i-propyl group, a n-butyl group, a s-butyl group, an i-butyl group, a t-butyl group, a n-pentyl group, and a n-hexyl group.
  • halogeno groups such as a fluoro group, a chloro group, a bromo group, and an iodo group
  • C1-6 alkyl groups such as a methyl group, an ethyl group, a n-propyl group, an i-propyl group, a n-butyl group, a s-but
  • the "C1-6 alkyl group" as G b may be linear or branched.
  • the alkyl group include a methyl group, an ethyl group, a n-propyl group, a n-butyl group, a n-pentyl group, a n-hexyl group, an i-propyl group, an i-butyl group, a s-butyl group, a t-butyl group, an i-pentyl group, a neopentyl group, a 2-methylbutyl group, a 2,2-dimethylpropyl group, and an i-hexyl group.
  • a substituent on the "C1-6 alkyl group" as G b include: halogeno groups such as a fluoro group, a chloro group, a bromo group, and an iodo group; a hydroxyl group; C1-6 alkoxy groups such as a methoxy group, an ethoxy group, a n-propoxy group, an i-propoxy group, a n-butoxy group, a s-butoxy group, an i-butoxy group, and a t-butoxy group; C1-6 haloalkoxy groups such as a 2-chloro-n-propoxy group, a 2,3-dichlorobutoxy group, and a trifluoromethoxy group; and halo-substituted, C1-6 haloalkyl-substituted, C1-6 haloalkoxy-substituted or unsubstituted C6-10 aryl group, such as a phenyl group
  • an arrow indicates a binding position.
  • p 1 indicates the number of methylenes in parentheses and is 0 or 1, preferably 1
  • p 2 indicates the number of methylenes in parentheses and is an integer of 0 to 2, preferably 1.
  • the cyclic amino group of formula (II-c) is represented by formula (II-c-1), when p 1 is 1 and p 2 is 1.
  • X 1 indicates a substituent on the cyclic amino group, and is a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a hydroxyl group, a substituted or unsubstituted C1-6 alkylsulfonyloxy group, or a substituted or unsubstituted C1-6 alkylthio group
  • m indicates the number of X 1 and is an integer of 0 to 4.
  • halogeno group substituted or unsubstituted C1-6 alkyl group
  • substituted or unsubstituted C1-6 alkylthio group substituted or unsubstituted C1-6 alkylthio group
  • C1-6 alkylsulfonyloxy group examples include a methylsulfonyloxy group, an ethylsulfonyloxy group, and a t-butylsulfonyloxy group.
  • a substituent on the "C1-6 alkylsulfonyloxy group” include halogeno groups such as a fluoro group, a chloro group, a bromo group, and an iodo group.
  • Y' represents a substituted or unsubstituted C1-6 alkylcarbonyl group, a substituted or unsubstituted C1-6 alkoxycarbonyl group, a group of R g' R h N-CO-, a group of R g' R h N-CS-, a group of R g' R h N-CO-CO-, a substituted or unsubstituted C1-6 alkylsulfonyl group, or a group of R g' R h N-SO 2 -, R g' represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, or a substituted or unsubstituted C6-10 aryl group, R h represents a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group, and R g' and R h may
  • Examples of the "C1-6 alkylcarbonyl group" as Y' include an acetyl group, and a propionyl group.
  • C1-6 alkoxycarbonyl group examples include a methoxycarbonyl group, an ethoxycarbonyl group, a n-propoxycarbonyl group, an i-propoxycarbonyl group, and a t-butoxycarbonyl group.
  • C1-6 alkylsulfonyl group examples include a methylsulfonyl group, an ethylsulfonyl group, and a t-butylsulfonyl group.
  • a substituent on the "C1-6 alkylcarbonyl group", “C1-6 alkoxycarbonyl group”, or “C1-6 alkylsulfonyl group” as Y' include halogeno groups such as a fluoro group, a chloro group, a bromo group, and an iodo group.
  • R g' represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, or a substituted or unsubstituted C6-10 aryl group
  • R h represents a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group
  • R g' and R h may be combined to form a substituted or unsubstituted C3-6 alkylene group.
  • Examples of the "C1-6 alkyl group" as R g' and R h include a methyl group, an ethyl group, a n-propyl group, a n-butyl group, a n-pentyl group, a n-hexyl group, an i-propyl group, an i-butyl group, a s-butyl group, a t-butyl group, an i-pentyl group, a neopentyl group, 2-methylbutyl group, a 2,2-dimethylpropyl group, and an i-hexyl group.
  • Examples of a substituent on the "C1-6 alkyl group” include halogeno groups, C1-6 alkoxy groups, C1-6 haloalkoxy groups, and a cyano group.
  • Examples of the "C1-6 alkoxy group" as R g' include a methoxy group, an ethoxy group, a n-propoxy group, an i-propoxy group, a n-butoxy group, a s-butoxy group, an i-butoxy group, and a t-butoxy group.
  • Examples of a substituent on the "C1-6 alkoxy group” include halogeno groups, C1-6 alkoxy groups, C1-6 haloalkoxy groups, and a cyano group.
  • Examples of the "C6-10 aryl group" as R g' include a phenyl group, and a naphthyl group.
  • Examples of a substituent on the "C6-10 aryl group” include halogeno groups, C1-6 alkyl groups, C1-6 haloalkyl groups, C1-6 alkoxy groups, C1-6 haloalkoxy groups, and a cyano group.
  • Examples of the "C3-6 alkylene group" formed by combining R g' and R h include a trimethylene group, a tetramethylene group, and a pentamethylene group.
  • Examples of a substituent on the "C3-6 alkylene group” include halogeno groups such as a fluoro group, a chloro group, a bromo group, and an iodo group; and C1-6 alkyl groups such as a methyl group, an ethyl group, a n-propyl group, an i-propyl group, a n-butyl group, a s-butyl group, an i-butyl group, a t-butyl group, a n-pentyl group, and a n-hexyl group.
  • halogeno groups such as a fluoro group, a chloro group, a bromo group, and an iodo group
  • C1-6 alkyl groups such as a methyl group, an ethyl group, a n-propyl group, an i-propyl group, a n-butyl group, a s-buty
  • R g' R h N-CO- examples include a N-methylaminocarbonyl group, a N-isopropylaminocarbonyl group, a N,N-dimethylaminocarbonyl group, a N-ethyl-N-methylaminocarbonyl group, a N-methoxy-N-methylaminocarbonyl group, a pyrrolidine-1-carbonyl group, a N-(4-chlorophenyl)aminocarbonyl group, and a N-(4-chlorophenylmethyl)aminocarbonyl group.
  • R g' and R h means the same groups as those mentioned above.
  • R g' R h N-CS- examples include: mono C1-6 alkylamino(thiocarbonyl) groups, such as a N-methylamino(thiocarbonyl) group, a N-ethylamino(thiocarbonyl) group, a N-n-propylamino(thiocarbonyl) group, a N-i-propylamino(thiocarbonyl) group, a N-t-butylamino(thiocarbonyl) group; and di C1-6 alkylamino(thiocarbonyl) groups such as a N,N-dimethylamino(thiocarbonyl) group.
  • mono C1-6 alkylamino(thiocarbonyl) groups such as a N-methylamino(thiocarbonyl) group, a N-ethylamino(thiocarbonyl) group, a N-n-propylamino(thiocarbonyl) group, a N-i-propyla
  • R g' and R h mean the same groups as those mentioned above.
  • R g' R h N-CO-CO- examples include: mono C1-6 alkylaminooxalyl groups, such as a N-methylaminooxalyl group, a N-ethylaminooxalyl group, a N-n-propylaminooxalyl group, a N-i-propylaminooxalyl group, and a N-t-butylaminooxalyl group; and di C1-6 alkylaminooxalyl groups such as a N,N-dimethylaminooxalyl group.
  • R g' and R h mean the same groups as those mentioned above.
  • Examples of the group of R g' R h N-SO 2 - include a N-methylaminosulfonyl group, a N,N-dimethylaminosulfonyl group, a N-ethyl-N-methylaminosulfonyl group, a N-methoxy-N-methylaminosulfonyl group, a pyrrolidin-1-yl sulfonyl group, a N-(4-chlorophenyl)aminosulfonyl group, and a N-(4-chlorophenylmethyl)aminosulfonyl group.
  • Y' represent a substituted or unsubstituted Cl-6 alkoxycarbonyl group, a substituted or unsubstituted C1-6 alkylsulfonyl group, or a group of R g' R h N-SO 2 -, R g' represent a substituted or unsubstituted C1-6 alkyl group, and R h represent a substituted or unsubstituted C1-6 alkyl group.
  • Ar in the formula (I) is preferably a substituted or unsubstituted phenyl group.
  • a compound of formula (I-a) is mentioned.
  • R 1 , R 2 , R 3 , X 2 , and Y mean the same groups as those in the formula (I), respectively.
  • X 3 indicates a substituent on a phenyl group, and n indicates the number of the substituent and is an integer of 0 to 5.
  • substituent on the phenyl group examples include the same substituents as those mentioned as the "substituents on a C6-10 aryl group" for Ar mentioned above.
  • Salts of the compound (I) are not particularly limited in the case of agriculturally or horticulturally acceptable salts.
  • examples thereof include salts of inorganic acids such as a hydrochloric acid or a sulfuric acid; salts of organic acids such as an acetic acid or a lactic acid; salts of alkali metals such as lithium, sodium or potassium; salts of alkaline earth metals such as calcium or magnesium; salts of transition metals such as iron or copper; and salts of organic bases such as ammonia, triethylamine, tributylamine, pyridine, or hydrazine.
  • the compound (I) or the salts of the compound (I) are not particularly limited by the preparation process thereof. Salts of the compound (I) may be obtained from the compound (I) by known methods. For example, a compound (I) or a salt of the compound (I) according to the present invention may be obtained by the process described in Examples, or the like.
  • the cyclic amine compound according to the present invention (hereinafter, may be referred to as “compound according to the present invention”) has excellent control effects against pests such as various agricultural insect pests and acarians that affect plant growth.
  • the compound according to the present invention is a highly safe compound as it has no phytotoxicity against crop plants and low toxicity to fish and warm-blooded animals.
  • the compound according to the present invention is useful as an active ingredient of an insecticide or acaricide.
  • the compound according to the present invention has excellent control effects not only on susceptible strains but also on insect pests of various resistant strains and even acarians of acaricide-resistant strains.
  • the compound according to the present invention has excellent control effects against ectoparasites that cause harm to humans or livestock.
  • the compound according to the present invention is a highly safe compound as it has low toxicity to fish and warm-blooded animals.
  • the compound according to the present invention is useful as an active ingredient of an ectoparasite-control agent.
  • the compound according to the present invention shows efficacy in all developmental stages of organisms to be controlled, and exhibits excellent control effects against eggs, nymphs, larvae, pupae, and adults of acarians or insects, for example.
  • a pest control agent, insecticide or acaricide according to the present invention contains at least one selected from the cyclic amine compounds according to the present invention, as an active ingredient thereof.
  • the amount of the compound according to the present invention contained in the pest control agent, insecticide or acaricide according to the present invention is not particularly limited, provided that pest control effects are exhibited.
  • the pest control agent, insecticide or acaricide, according to the present invention be applied to cereals; vegetables; root vegetables; potatoes; flowers and ornamental plants; fruit-bearing trees, foliage plants; trees, such as tea, coffee, or cacao; feed crops; lawn grasses; or plants such as cotton.
  • the pest control agent, insecticide or acaricide may be applied to any portions, such as leaves, stems, stalks, flowers, buds, fruits, seeds, sprouts, roots, tubers, tuberous roots, shoots, or slips.
  • the pest control agent, insecticide or acaricide, according to the present invention is not particularly limited by the species of the plant to be applied. Examples of the plant species include original species, varieties, improved varieties, cultivars, mutants, hybrid bodies, and gene recombinants (GMO).
  • the pest control agent according to the present invention may be used to control various agricultural insect pests and acarians by conducting seed treatment, foliage application, soil application, or submerged application.
  • the pest control agent, insecticide or acaricide, according to the present invention may further contain additional components different from the compound according to the present invention.
  • additional components include conventional carriers available to conduct formulation.
  • additional components include conventional fungicides, insecticides, acaricides, nematicides, soil pest control agents, plant regulatory agents, herbicides, synergists, fertilizers, soil improvement agents, and animal feeds. There is a case where synergistic effects are exhibited by formulating such additional components.
  • insecticides acaricides, nematicides, soil insect pest control agents, and anthelmintic agents which can be mixed or used with the pest control agent, insecticide or acaricide, according to the present invention are shown below.
  • fungicides which may be mixed or used with the pest control agent, insecticide or acaricide according to the present invention are shown below.
  • plant regulatory agents which can be mixed or used with the pest control agent, insecticide or acaricide, according to the present invention are shown below.
  • An ectoparasite control or expellant agent according to the present invention contains at least one selected from the group consisting of the compounds according to the present invention, as an active ingredient thereof.
  • the ectoparasite control or expellant agent according to the present invention is excellent in controlling ectoparasites that cause harm to humans or livestock.
  • the ectoparasites parasitize the host animals, especially parasitize the body or the skin of warm-blooded animals or fish. More specifically, the ectoparasites parasitize the back, armpit, underbelly, inner thigh or the like of the host animals and obtain nutritional sources such as blood or dandruff from the animals to live. Examples of the ectoparasites include acarians, lice, fleas, mosquitoes, stable flies, flesh flies, Japanese fishlouse (Argulus japonicas) and the like.
  • Examples of the host animals to be treated with the ectoparasite control or expellant agent according to the present invention include warm-blooded animals such as pet animals such as dog or cat; pet birds; farm animals such as cattle, horse, pig, and sheep; domestic fowls. Additional examples thereof include: fish such as salmon, trout, puffer, carp, and goldfish; and insects such as honey-bee, stag beetle, and unicorn beetle.
  • the ectoparasites live in and on the host animals, especially warm-blooded animals. More specifically, the ectoparasites parasitize the back, armpit, underbelly, inner thigh or the like of the host animals and obtain nutritional sources such as blood or dandruff from the animals to live.
  • the ectoparasite control or expellant agent according to the present invention may be applied by a known veterinary method (topical, oral, parenteral or subcutaneous administration).
  • a known veterinary method topical, oral, parenteral or subcutaneous administration.
  • the method include: a method in which a tablet, capsule or feed mixed with the ectoparasite control or expellant agent are orally administered to the animals; a method in which an immersion liquid, suppository or injection (intramuscular, subcutaneous, intravenous, intraabdominal or the like) is administered to the animals; a method in which an oil-based or aqueous liquid preparation is topically administered by conducting spraying, pouring on, spotting on or the like; and a method in which the ectoparasite control agent is topically administered to the animals by attaching a collar, an ear tag or the like made by molding, into an appropriate form, a mixture obtained by kneading the ectoparasite control agent into a resin
  • Fleas belonging to the family Pulicidae such as Ctenocephalides canis and Ctenocephalides felis of Ctenocephalides spp.; fleas belonging to the family Tungidae, fleas belonging to the family Ceratophyllidae, and fleas belonging to the family Leptopsyllidae.
  • the compound according to the present invention exhibits an excellent effect of controlling insect pests that have a sting or venom that can harm humans or livestock, insect pests carrying various pathogens / pathogenic bacteria, or insect pests that impart a discomforting sensation to humans (such as toxic insect pests, sanitary insect pests, or unpleasant insect pests).
  • Sawflies belonging to the family Argidae wasps belonging to the family Cynipidae, sawflies belonging to the family Diprionidae, ants belonging to the family Formicidae, wasps belonging to the family Mutillidae, and wasps belonging to the family Vespidae.
  • Formulation examples of the pest control agent, insecticide, acaricide, or ectoparasite control or expellant agent are shown below.
  • the present invention is not limited to these formulation examples.
  • the terms “part” and “%” in the formulation examples are indicated based on mass.
  • a compound according to the present invention was dissolved in an organic solvent to obtain a solution.
  • the solution was sprayed on 94 parts of kaolin and 1 part of white carbon, followed by evaporating the solvent under reduced pressure to obtain granules.
  • the granules may be mixed with animal feed to be used.
  • 0.1 to 1 part of a compound according to the present invention and 99 to 99.9 parts of peanut oil were mixed uniformly, and then filter-sterilized using a sterilizing filter to obtain an injection agent.
  • Ethyl 5-cyano-2-(difluoromethyl)-6-hydroxynicotinate (9.94 g) was suspended in dichloromethane (200 ml), and then N,N-dimethylformamide (0.75 g) and oxalyl chloride (26 g) were added thereto under ice-cooling. Then, the mixture was heated to reflux for 3 hours. The resultant solution was concentrated under reduced pressure, and then extracted with an ethyl acetate. The extracted phase was washed sequentially with a saturated aqueous sodium hydrogen carbonate solution and then with a saturated saline, followed by drying the resultant with anhydrous magnesium sulfate.
  • Ethyl 6-chloro-5-cyano-2-(difluoromethyl)-nicotinate (3.92 g) and 4-trifluoromethylphenylboronic acid (4.28 g) were dissolved in a mixture solvent composed of toluene (80 ml) and water (8 ml).
  • Potassium carbonate (4.77 g) and dichlorobis[di-t-butyl(p-dimethylaminophenyl)phosphino]palladium (II) (0.53 g) were added thereto, and then the mixture was heated to reflux for 8 hours under nitrogen atmosphere.
  • the resultant soulution was cooled to room temperature, poured into water, and then extracted with an ethyl acetate.
  • the extracted phase was washed with saturated saline, and then dried with anhydrous magnesium sulfate.
  • the solvent was distilled off under reduced pressure, and the resultant residue was purified by silica gel column chromatography (eluent: n-hexane / ethyl acetate) to obtain the target compound (5.04 g, at a yield of 91%).
  • the NMR result of the target compound is shown below. 1 H-NMR (CDCl 3 , ⁇ ppm) 1.41 (3H, t), 4.43 (2H, q), 6.91 (1H, t), 7.82 (2H, d), 8.09-8.11 (3H, m).
  • the extracted phase was washed sequentially with water, and then with saturated saline, followed by drying the resultant with anhydrous magnesium sulfate.
  • the solvent was distilled off under reduced pressure, and the resultant residue was purified by silica gel column chromatography (eluent: n-hexane / ethyl acetate) to obtain the target compound (0.3 g, at a yield of 53%).
  • the solvent was distilled off under reduced pressure, and the resultant residue was purified by silica gel column chromatography (eluent: n-hexane / ethyl acetate) to obtain the target compound (0.04 g, at a yield of 75%).
  • the NMR result of the target compound is shown below.
  • Tables 1 to 6 Some compounds according to the present invention, prepared in the same manner as the above-mentioned examples, are shown in Tables 1 to 6.
  • Table 1 shows substituents of compounds of formula (I-a-1). n in the formula indicates the number of substituents (X3) on a benzene ring.
  • Table 2 shows substituents of compounds of formula (I-a-2), Table 3 shows substituents of compounds of formula (I-a-3), Table 4 shows substituents of compounds of formula (I-a-4), Table 5 shows substituents of compounds of formula (I-a-5), and Table 6 shows substituents of compounds of formula (I-a-6).
  • the physical properties column of each table shows the properties, melting point (m.p.) or refractive index (n D ).
  • Ph represents a phenyl group
  • t Bu represents a t-butyl group
  • Et represents an ethyl group
  • Me represents a methyl group
  • i Pr represents an isopropyl group
  • c Hex represents a cyclohexyl group
  • n Bu represents a n-butyl group
  • n Pr represents a n-propyl group
  • c Pr represents a cyclopropyl group.
  • An arrow indicates a binding position.
  • the resultant solution was poured into ice-water and then extracted with chloroform, followed by conducting washing sequentially with water and then with saturated saline. Then, the resultant was dried with anhydrous magnesium sulfate. The solvent vas distilled off under reduced pressure, and the resultant residue was purified by silica gel column chromatography (eluent: n-hexane / ethyl acetate) to obtain the target compound (0.12g, at a yield of 32%).
  • the NMR result of the target compound is shown below.
  • the resultant solution was poured into ice-water and then extracted with chloroform, followed by conducting washing sequentially with water and then with saturated saline. Then, the resultant was dried with anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resultant residue was purified by silica gel column chromatography (eluent: n-hexane / ethyl acetate) to obtain the target compound (0.13 g, at a yield of 38%).
  • the NMR result of the target compound is shown below.
  • Table 7 shows substituents of compounds of formula (I-b). n in the formula indicates the number of substituents (X3) on a benzene ring.
  • the physical properties column of Table 7 shows the properties, melting point (m.p.) or refractive index (n D ).
  • Me represents a methyl group
  • Ph represents a phenyl group.
  • An arrow indicates a binding position.
  • Table 7 No. Q R 1 R 3 (X 3 )n Physical properties A-1 CN OF 2 H 4-CF 3 m.p.
  • T-butyl 4-(5-cyano-2-(trifluoromethyl)-6-(4-(trifluoromethyl)phenyl)nicotinoyl) piperazine-1-carboxylate (1.0 g) was dissolved in 1,4-dioxane (9 ml). A 1,4-dioxane solution of 4M hydrochloric acid (2.4 ml) was added thereto, and then stirred at room temperature overnight.
  • test examples show that the compound according to the present invention is useful as an active ingredient of an insecticide, acaricide or ectoparasite control agent.
  • emulsion (I) Five female adults of Tetranychus kanzawai from Okayama Prefecture were left on the primary leaves of mung beans. Then, the emulsion (I) was diluted with water such that the concentration of the compound became 125 ppm by mass to obtain a test agent. The test agent was sprayed on the mung beans and air-dried. Thereafter, the mung beans were placed in a thermostatic chamber at a temperature of 25°C and a humidity of 65%. The acarian survival was investigated 10 days after spraying. The test was repeated twice.
  • Table 9 The compounds shown in Table 9 were subjected to the efficacy test against Tetranychus kanzawai. All of the compounds exhibited, against Tetranychus kanzawai, an acaricidal rate of 90% or more.
  • Table 9 No. a-3 a-47 a-82 a-105 a-133 b-18 b-43 e-3 A-15 a-11 a-49 a-83 a-107 a-134 b-19 b-44 e-5 A-18 a-12 a-50 a-84 a-110 a-135 b-21 b-45 e-6 A-26 a-14 a-51 a-85 a-112 a-136 b-22 b-46 e-7 B-2 a-15 a-52 a-86 a-113 a-137 b-23 b-47 e-8 B-3 a-18 a-53 a-87 a-114 a-138 b-24 b-48 e-9 B-4
  • Common beans were grown in a 3-sun pot and eight female adults of Tetranychus urticae from Aomori Prefecture were left on the primary leaves thereof.
  • the emulsion (I) was diluted with water such that the concentration of the compound according to the present invention became 125 ppm by mass.
  • the diluent was sprayed on the common beans.
  • the common beans were placed in a thermostatic chamber at a temperature of 25°C and a humidity of 65%.
  • the acarian survival was investigated 10 days after spraying. The test was repeated twice.
  • Table 10 The compounds shown in Table 10 were subjected to the efficacy test against Tetranychus urticae. All of the compounds exhibited an acaricidal rate of 90% or more.
  • Table 10 No. a-3 a-78 a-118 a-152 a-197 b-26 b-60 b-93 B-2 a-11 a-79 a-119 a-153 a-198 b-28 b-61 b-94 B-4 a-22 a-80 a-120 a-154 a-199 b-29 b-62 b-95 a-25 a-81 a-121 a-155 a-200 b-30 b-63 c-1 a-26 a-82 a-122 a-156 a-201 b-31 b-64 c-2 a-27 a-83 a-124 a-157 a-202 b-32 b-65 c-3 a-30 a-84 a-125 a-
  • Table 11 The compounds shown in Table 11 were subjected to the efficacy test against Tetranychus urticae. All of the compounds exhibited a control value of 90% or more. Table 11 No. a-32 a-53 a-54 a-56 a-57 a-69
  • the emulsion (I) was diluted with water such that the concentration of the compound according to the present invention became 500 ppm by mass.
  • 4 ml of the diluent was irrigated at the base of a seedling of common bean planted in a cell, and then the cell was placed in a thermostatic chamber at a temperature of 25°C and a humidity of 60%.
  • the common bean was transferred to a 3-sun pot, and then 10 female adults of Tetranychus urticae were left, followed by placing the pot in a thermostatic chamber at a temperature of 25°C and a humidity of 60%.
  • the acarian survival was investigated.
  • the control value was calculated in accordance with the following formula.
  • Control value % 100 ⁇ Nt / Nc ⁇ 100 Nc: the number of surviving acarians at untreated area; Nt: the number of surviving acarians at treated area
  • Table 12 The compounds shown in Table 12 were subjected to the efficacy test against Tetranychus urticae. All of the compounds exhibited a control value of 90% or more. Table 12 No. a-32 a-53 a-54 a-56 a-57 a-69
  • the compound according to the present invention is a compound that exhibits pest control effects, particularly insecticidal effects, acaricidal effects, or ectoparasite control effects, without causing harmful effects on plants, and provides less toxicity on humans, animals, or fish, and fewer effects on the environment.
  • the cyclic amine compound according to the present invention makes it possible to control pests that cause problems in agricultural crops and hygiene.
  • the cyclic amine compound according to the present invention particularly makes it possible to control agricultural insect pests and acarians at a low concentration effectively.
  • the cyclic amine compound according to the present invention makes it possible to effectively control ectoparasites that cause harm to humans or livestock.

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WO2022219146A3 (en) * 2021-04-16 2023-04-06 Syngenta Crop Protection Ag Pyridine derivatives and their use as pesticide
WO2024056732A1 (en) * 2022-09-16 2024-03-21 Syngenta Crop Protection Ag Pesticidally active cyclic amine compounds

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UY38885A (es) 2019-09-20 2021-04-30 Syngenta Crop Protection Ag Compuestos de azetidinil-, pirrolidinil-,piperdinil- o piperazinil-piridinil carbonilo pesticidamente activos
CN115210218B (zh) 2020-02-11 2025-05-16 先正达农作物保护股份公司 杀有害生物活性的环胺化合物
JP2023077429A (ja) * 2020-04-22 2023-06-06 日本曹達株式会社 ベンズアミド化合物および有害生物防除剤
WO2021219513A1 (en) 2020-04-28 2021-11-04 Basf Se Pesticidal compounds
BR112023019828A2 (pt) 2021-03-30 2023-11-07 Syngenta Crop Protection Ag Compostos de amina cíclica pesticidamente ativos
CN114195678A (zh) * 2021-12-24 2022-03-18 江苏七洲绿色科技研究院有限公司 一种中间体、其制备方法及用其制备3-二氟甲基-1-甲基吡唑-4-甲酸乙酯的方法
CN118451068A (zh) 2021-12-30 2024-08-06 上海翰森生物医药科技有限公司 三并环类衍生物抑制剂、其制备方法和应用
CN120225508A (zh) 2022-11-24 2025-06-27 先正达农作物保护股份公司 杀有害生物活性的环胺化合物
AU2024366771A1 (en) 2023-10-27 2026-04-16 Syngenta Crop Protection Ag Pesticidally active cyclic amine compounds

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JP2017159583A (ja) 2016-03-10 2017-09-14 凸版印刷株式会社 防湿化粧板および建材、化粧板、化粧シート
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WO2024056732A1 (en) * 2022-09-16 2024-03-21 Syngenta Crop Protection Ag Pesticidally active cyclic amine compounds

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